


Third Time's A Charm

by TeaseMe2



Category: Arrow (TV 2012)
Genre: F/M
Language: English
Status: Completed
Published: 2016-01-19
Updated: 2016-01-19
Packaged: 2018-05-15 00:30:05
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 11,054
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5764795
Author URL: https://archiveofourown.org/users/TeaseMe2/pseuds/TeaseMe2
Summary: <blockquote class="userstuff">
              <p>They say third time's a charm...But nobody ever told Felicity she would babble like a silly 'fangirling' teen the third time she encountered the reformed playboy moonlighting as a vigilante. Nor when he gave her hints of his feelings or when he asked her to stand by him. Little Oliver/Felicity drabbles.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Just a silly little drabble to add to the olicity fandom. I wrote this during hiatus, so forgive me for any sign of salmon ladder withdrawal you might spot in there. I rated this fic M, so I'd be free to use the word 'fuck' whenever I want. But it is safe to read at work, don't worry.
> 
> I own nothing but my ideas and words, everything else belongs to its rightful owner. Enjoy & thanks for reading.

The first time Felicity Smoak heard about Oliver Queen, her roommate was fangirling over Starling City's very own playboy billionaire in their MIT dorm. She read the Starz City online, the go to tabloid when you wanted to keep up with the town's celebrity, the one percent-er of this world and various starlets, actors and heirs who ended up being front page news. The man, she had to admit, was damn fine. He was photographed after an altercation with a paparazzi, his lower lip split and a trickle of blood running down his chin. His hair fell in front of his bloodshot eyes, barely hiding the man's drunken state. There was a brunette and a red head, both wearing dresses that seemed too slutty for any public event, and much more suited for stripping in a high end gentlemen club, she remembered thinking.

Felicity could see the appeal of Mr Queen, duh, she wasn't blind, and the man could probably charm the pants off of every lady in town. Hell, any person really, if the comments section was anything to go by. Men and women alike seemed to fawn over this particular heir, no matter how bad his behavior got. Everybody loves a bad boy and this one got more attention than any other, having been expelled from four different colleges for alcohol consumption, drunken pranks, nudity, sexual compulsions recalled the article her roommate Alicia was reading aloud.

'Sexual compulsions? What the hell does that even mean,' asked the resident geek to her gymnast friend.

'I heard he got busted in the library while having a threesome-'

'Geez, some people have no self respect.'

'Oh, come on, Felicity, live a little, the man is gorgeous, he's sex on legs, of course he's gonna have beautiful dirty sex with different women, fuck what I wouldn't do to have him in my bed, I'm telling you Fel, even you wouldn't be able to resist that.'

'Beautiful, dirty sex, really?!'

'Fuck yes little miss virgin, the kind that leaves you sweaty, tired and fully satisfied.'

Felicity tsk-ed at her and went back to studying, paying Oliver Queen no more attention as the other girl lusted over the now half naked man on her screen.

The second time the man registered on her radar, she was having coffee with her tablet for companion, just days after her graduation from MIT. She sat with her back to the windows, oblivious to the commotion outside as she reviewed the five firms offering her a first job, though a bit miffed they were only five of them, as her tutor told her tales of countless companies vying for his attention back in the day when he graduated top of his classes throughout her days on scholarship. Oh well, must be the state of the economy she thought with a sigh, clicking her way through Queen Consolidated website.

Fondly, she remembered the days she spent with her gossiping roommate, the only reason she even kept up with Starling City elite. Last she heard, Oliver Queen died in a shipwreck in the beginning of her MIT days, leaving Alicia and billions of women throughout the country heartbroken at the loss of the magnificent body and overall slutty bad boy the Queen heir proved to be during his 22 years on Earth. Really, women mourned for months, the Queen family had to hire security to manage the weeping females on his funeral, which astounded Felicity, as these women were mostly grown ups with jobs, families and responsibility. Yet, even five years later, the mourners still missed the former golden boy and organized a 'Remember Oliver Queen' day, if you can believe such a ridiculous thing.

They had a community of sorts and every year on the day of his passing people would post pictures, poems or RPF about the poor guy. Alicia was, of course, a prominent member of this cult as Felicity jokingly called it every time her former MIT acolyte brought up the deceased playboy. Thankfully, since her friend had a newborn baby, she spent more time talking about diapers, mommy blues and baby steps than dead heirs. Though she did name her daughter Olivia, much to her husband's amusement and his mother delight. Poor grandma had no idea her daughter-in-law intended it as a tribute to a pretty face, hard body and former infatuation of her youth rather than honoring her husband's mother. And she never would, that was her husbands only stipulation prior to agreeing to name his baby after a celebrity. And coincidentally, his mother.

Felicity softly smiled as she gathered her things in her oversized bag, finishing her coffee while her thoughts derailed to her goddaughter. Turning around to exit the quaint coffee shop, she collided into an old man and his cane, barely avoiding the floor while the grandpa held onto a chair to steady himself.

As she got up, the TV flashed its breaking news banner, interrupting the documentary previously airing to show Oliver Queen in all his drunken stupor, with headlines reading 'LOST BILLIONAIRE FOUND'.

Approximately two minutes after that, Felicity almost lost all hearing capacities when her friend screeched endlessly in her ear about her favorite playboy coming back from the dead.

Third time's a charm, they say. They just don't tell you about the hot guy who was stranded on a godforsaken island for five years, his abs, his voice, his charm or your propensity for awkward exchanges. And they most definitely never tell you about your blubbering mess of introductions...

'Felicity Smoak?Hi, I'm Oliver Queen'

'Of course, I know who you are, you're Mr Queen-'

'No, Mr Queen was my father.'

'Right, but he's dead...I mean he drowned...But you didn't which means you could come down to the IT department and listen to me babble...which will end in 3...2...1...'

Fuck, that was painful. She agreed to help him with his 'latte spill' aka bullet holes ridden laptop but could not bite back her sarcastic comments about it nor his 'Shakespearean drama family thing'.

The man seemed entertained by her lack of filter and smirked at her while laying on the charm heavily to get his way. Which was fine. Like any sane female with a healthy sexual drive, she could not help but be aroused by the man. It took her years, but she finally understood why he inspired such fangirling in every hot blooded female or homosexual man.

The man was a walking sex addiction waiting to happen.

One look at that, with his voice and whole demeanor and one could not help but want more. Much more than a really awkward exchange with this very attractive male specimen and sadly, Felicity had to admit to herself, she was no exception.

Maybe third time's really a charm...as she could not help but lend her IT expertise to the Queen Consolidated heir, learning how bad he was at lying along the way. The man had a pull, he seemed honest no matter how many ridiculous lies he tried to sell her, there was just something about him, drawing her to him. She asked if she could trust him to keep Walter Steele's secret, saved his life, invested her time and safety in his crazy vigilante crusade along with Diggle. They became his support unit, 'team arrow' as she liked to call them in her head. She never regretted her choice to stick with the reformed playboy, no matter how dangerous things got or how many former island flames of his were brought up. She acted as his right hand man, thwarted Miss Rochev's plans to take over his company, helped him ensure the safety of their city and its citizen.

She felt like a super hero sidekick, with a skirt and dyed blond hair but still, Oliver Queen and his alter ego gave her a purpose. She mattered. And helped people, even if they would never know her as more than Oliver Queen's IT girl first, his EA second and much later his life partner.

First time he asked her out on a date, she thought the man was bipolar. Barely a month after their trip to Russia, she met Barry Allen. Needless to say her crazy boss slash vigilante extraordinaire did not approve. At all. Oh, he played his part, inviting the young scientist to his mother welcome home from jail party- yes, apparently, Queens threw such parties... but he was short with the young man, sizing him up from the other corner of the room, watching him fumble with dancing, stepping thrice on Felicity toes while he had to endure endless dance lesson as a kid, mother's orders, which made him a decent partner. Never mind that she forgave him his little outburst, here he was, practically sulking like a scorned little boy while the object of his affection was having the time of her life with a barely old enough to drink boyish man. After that crazy instance, his life got threatened – again- and she made a decision for him. While he needed her IT skills and had to see her every day at QC, he was short with her and stopped touching her. She missed that. A lot. Anyways barely a month after that, lo and behold, he actually apologized for acting like a self entitled jackass, her words. She scoffed at his date proposal and threw a shoe at him. Let it be said that when Oliver Queen wants something, he will not stop until he has it. He proved to be persistent and pestered her twice more until she gave him a chance. He tried much harder to get her to go public with him.

'Felicity, we've been dating for over six month, we've known each other for three years-' 'Almost' 'Right, almost. Well I think it's time-'

'Time for what?' she screeched, throwing him suspicious looks from her side of the bed 'I swear to God Oliver, if you're breaking up with me in my own bed, in my apartment, after I've just gave you-'

'I'm not breaking up with you, Felicity' he sighed and smiled softly at his Girl Friday, babbler extraordinaire and awkward exchanges expert. 'I'm trying to convince you to go public with me.' Felicity gave him a blank look, her mouth opened wide in shock and disbelief at her boss-vigilante-turned-sorta-boyfriend. 'Well, Miss Smoak, nothing to say to that?' His smirk was full on, taunting her into more babbling at what he considered a perfectly sound suggestion.

'What?! Oliver, no...Don't you understand? Public means in front of everyone, and I can't...I mean you know me, I'm not good at public. If I could only talk to you, Diggle and my babies, I would probably not have much more human interaction. Are you drunk-or high?Or sick maybe? That's why you're asking me that right? God, I can't help it...See?I'm a disaster. Why would you have such crazy notions in your head if you were in your right mind?Obviously you're not. Sane. I mean, of course you are, usually, sometimes...I mean...it's just, you know the double personality slash I've been stranded on an island and the toll...Maybe you're having a nervous breakdown?Oh my god don't. That would suck, I'd have to call 911 and they would find you here, in my bed, where you're not supposed to be, and that would be all over the news and trashy tabloids would skin me alive. And really, Oliver? You're a grown up now, you are supposed to project a new, improved image, did you not pay attention to our last meeting with Queen Consolidated PR person? I knew it! You were doing your fake notes routine again, weren't you?You have to stop that, I told you last time, I'm not your secretary, I'm your EA which is highly different. And you promised to try. Why would you...Now...I don't...Just...Public? Really Oliver? What are you thinking?And holy fuck, I'm still talking and you're laughing. Why are you not stopping me? Stop laughing, see this is why this is a terrible idea, Oliver. TERRIBLE idea. I'm not suited to go public with you, don't you see that? God, okay that will stop in 3...2...1'

Between laughing fits the reformed billionaire explained why this was such a good idea and surprisingly, after two more ambushes of the sort, one especially awkward in front of the board meeting through texts he pretended to send to Japan, Felicity agreed. But only after he threatened to yell his proposal in front of the whole shareholders board meeting. Thrice. Or as much as she would need to consent.

Years later, she would still pretend it was only to spare him the mortification of rejection, of course. It had nothing to do with the fact her heart was still racing after the third time he asked, still almost unbelievably stunning to her that such a man would choose her when he could have his pick of women and men pretty much everywhere he went.

And he would laugh at his wife, surrounded by their family, old and new, blood ties or not, still as enamored as the first three years he resisted the pull she held over him. Back when he still thought he could not let himself be with someone he could really care about.


	2. Chapter 2

**Notes for the Chapter:**

> I own nothing but my words and a lust for super heroes, violence and sexual chemistry. Sue me. No don't, really, I only own a crazy obsessive brain who won't shut up but everything else belongs to its rightful owner.

There was one thing Felicity Smoak never expected – well...besides being a vigilante sidekick of sorts, but who can ever prepare for that, right? - she couldn't phantom a day where her crazy billionaire extraordinaire would feel a tenth of the attraction she felt for him. Things like that did not happen to babbling, awkward IT specialists, especially not when they graduated top of their classes at MIT. It happened to beautiful, self-assured, composed beauties like Miss Laurel Lance, first love of said billionaire playboy or even her sister Sara, on rainy days, as a stand-in for aforementioned love interest of one Queen Consolidated heir but that's it.

Yet, sometimes the unexpected happens, two people collide and their world finds a way to merge into one. Not often, admittedly, which made Felicity stick to a great rule that never failed her before, whenever men were concerned: do not get your hopes up.

She did not fully understand until Russia how wise that was. It seemed things were going great between them, both at QC and on the Arrow front. Except for a few bumps along the way, they were making progress. Oliver was slowly starting to open up with both her and Diggle, their team was stronger than ever, they were beginning to move on from their guilt after the quake in the Glades. Her favorite green hooded vigilante had even started to forgive himself for Tommy's death. He was willing to try _another way_ with his crusade, attempt to be what this city really needed and what she surmised he really was right from the start, a hero.

The people of Starling City desperately needed someone to take a stand, to bring some balance into their corrupted lives. Justice needed to be served and Oliver Queen was just the man for it.

Hardened by five years on a hellish island, the man could never fear the city's elite, he had seen too much for that. They were but a bunch of corrupt cops, shady politicians and greedy one percent-ers. Nothing out of his league considering the things he had witnessed and done during his stint with the Bratva. Felicity could not help but wonder what else had happened to him during these years, ever since she heard the news on channel 7 about the return of the long lost Queen heir; she had been thinking about the hardships the man must have endured, back when she still thought he was but a very wealthy Robinson Crusoe with luck on his side.

Since then, her perception of luck morphed into a double-edged sword. She had also seen his scars.

His chest and back were lacerated with scarred tissue. Felicity would see them whenever Oliver would work out in the basement at Verdant, always shirtless as if she needed more incentive to lust after him.

She recognized some bullet holes, flogging and stabbing marks, yet the most prominent of them were certainly those she could not see.

Such torture would infringe a deeper mark than any scar upon his psyche. She expected it would not let his mind rest and supposed he would still have nightmares waking him up in the middle of the night, drenched in sweat after reliving the excruciating torments of his stranded self.

Though he would probably never mention it to any one but Diggle, she was pretty sure Oliver suffered from PTSD as many war veterans did, and what had he gone through if not a war of his own?

No one came back from the dead as he did, after five years spent on an ex Chinese imprisonment island without some trauma to show for it. Of course, Oliver had a knack for acting and he frequently used his playboy persona to divert people from the truth of his past but she knew.

Beyond the twisted imagery her mind could conjure, she was never one to go blindfolded on a crazy path. As far as Mr Queen knew, she was none the wiser regarding his past involvement with the Solntsevskaya Bratva -or at least he probably thought she had been satisfied with the half answers she had received, the evading both he and Diggle had done when she started to get curious...

 _Ah, if they only knew,_ she thought.

Come on, she was nothing if not a computer genius, that was her element, and what holds a computer? Yes, besides a motherboard, a hard drive, usb ports and graphic cards. That was just a means to an end. Mechanical progress leading to power. The real question is where does the power lies. One word answer, eleven letters, the thing that fascinated her since her most tender age about computers, the very thing that drew her to them.

They hold information, therefore knowledge. Creating the world wide web changed the world. Suddenly every piece of information, every trace each of us left somewhere in whatever capacity you can think of, each little footprint we made in this world connected together in a pattern we would watch grow up, evolve until it became everything. There is practically nothing you can't find on the internet and sifting through information, decoding encrypted files, scanning the internet to his hidden depth, the one most people never had access to was her _thing_ , the one single thing she excelled at. You better believe that after finding out a certain vigilante bleeding in her car and he proved to be none other than the Queen heir, she did her research.

Thoroughly.

Yes, that included backlogged encrypted conversations of various criminal organizations throughout the world, Bratva affiliates included. There was no fucking way, pardon her French, that she would go blind into anything. Felicity Smoak was never that kind of girl, the adventure prone, optimist, crazy blonde who got into crazy situations to get her blood pumping. Instead, she was the nice girl next door who never got into trouble into college -save for a night where she decided to let loose, have few drinks and party like a wild animal but let's just say that was a very short story, the ending of which proved that she was a very lightweight when Tequila, lemon and shots were involved...

Bottom line is the woman she had grown up into was much careful than her younger self, always calculating the probabilities of an action going wrong, analyzing the ripples it could produce, evaluating the results and so forth. Diggle got the full background check treatment first, but his record went just as far as she expected from an ex-soldier. Spotless track record during his Army days, never been in trouble with the law before or after that, the man was clean as a whistle on the personal side as well and the only thing his phone bills showed was that he cared way too much about his deceased brother's wife but nothing more interesting.

Very much unlike Oliver.

She spent a week end on the case of Mr Oliver Queen. And boy was she not disappointed by what she found. Amongst useless trashy information tabloids were more than willing to procure, including but not limited to compromising pictures, assaults reports against paparazzi -which she double checked with the legal records- and some unpaid tickets that she expected when dealing with the idle rich and their need for crazy entertainment, she found faint traces about a foreign appointed Bratva captain.

Let it be said that for the most part, those Russian Mafia boys were careful, but even they were no match for a good algorithm providing the right cypher to decode their strange code. They were smart and never said too much, only letting her glimpse into Oliver's Russian period, just enough to let her know that body count of his had started much earlier than his latest arrowing in Starling City.

Yet she never let on to either of her boys that she knew. Oliver would tell her in his own words whenever he felt ready to share. And if he didn't, at least she knew enough to put her conscience at ease.

The first time Oliver gave her an inclination towards his feelings for her was the day after Russia.

" _Because of the life that I lead...I just think that it's better to not...be with someone that I could really care about."_

It was just after what she called the Russiangate in her head, when she knocked at his door to find out he had slept with Miss Rochev when said woman walked out his door. Hurt, disbelief, disappointment, you name it, she had felt it deep in her bones, sticking to her like a stench that would never go away, leaving a mark of its own. She was angry. That woman had all the markings of a backstabbing bitch waiting to sink her claws and suck the life out of everything she saw.

It made no sense whatsoever for him to pick her out of the millions of women Oliver could have slept with on that fateful day.

But hey, too bad, his dick obviously just had to choose this single one. The one that could discover the true purpose of their Russian escapade, the single female who could ruin them all in a snap of her fingers. Well women of this universe fear not, apparently Oliver Queen's cock did not discriminate. Hell, it would probably fuck everything in sight provided it was a warm blooded woman willing to open her legs for Junior.

God, what a massive fuck up. Bitterly, she thought back when the faint strings of hope had planted their seed in her mind, when he had some tender touches for her on occasion or when he would give her a true smile, rather than his usual fake smirk. Against her better instincts, she had to admit she had started to believe things were changing between them,albeit slowly but they were evolving nevertheless. Yeah, right. Should have known better, obviously. She would not abandon her boys and more importantly her babies hidden in the club's basement on the account of her imaginative mind and ever growing lust, no, what they were doing was important enough for her to bite her tongue, lock up her crazy feelings and move the fuck on.

The only thing she had perhaps underestimated was the lack of control she obviously held over her rampant feelings.

Moving on is never as easy as they say, never mind when you spend more time together than apart, at the office, in the basement...He looked the same while she felt a tiny bit crushed. She buried it under layers of self-preservation and respect, but she still felt hurt by his asshole, playboy act.

The next time she sneaked a peak at his feelings, it was the look in Oliver's face when he came to rescue her from the Count's delirious crutches. He had killed for her, that night. The crazy drug enthusiast would never unleash such a dangerous drug on any city much less breathe again after his fall from QC building, his body obliterated by three green arrows. Now while she held no remorse over his demise, for the man was a psychotic delusional maniac, Felicity still felt guilty. For her favorite vigilante's broken promises to a dead brother he could not save, for the toll it took on his soul with each criminal life added to the balance of his body count, for all that she felt tremendous regret.

There were apologies, looks and hushed understanding between them but still, the guilt remained. She never wanted to be the one who caused him pain. He rested enough weight on his sole shoulders, those shadows sometimes overcasting his light, the one mark he persisted on inflicting to himself. The man would never forgive himself for many things, she knew it was part of what made him so great at what he did, his ever present conscience eating the last part of innocence away with every lethal arrow his bow would deliver.

She never thought it was easy for him, contrary to what he thought when he came back from his latest time on Lian Yu after the Undertaking. That's why she felt so guilty for her carelessness, because the price had been to high for him, despite his reinsurance, Felicity would never put him in that position again if she could help it.

After that terrifying night, Felicity felt a shift in their dynamic, thought it might mend the bridge caused by the awkwardness of her feelings, unspoken thoughts and refrained sentiments between them but it never came. They remained in limbo, both knowing what the other felt and trying as best as they could to put it aside and let it go. Then, came bright, young and awkward Barry Allen.

The assistant forensic hailing from Central City had seemed a safe bet for her. Sure, he was no Oliver, but that was good. Change was needed and Barry would do just fine to help her move on. Yeah, another one of her bright ideas. There was no stand-in possible for someone like her favorite CEO and his vigilante alter ego, not even when the scientist did save him and never told anyone about the Arrow's true identity. Her heart had its sight set on one delicious Mr Queen and it had no plans to content itself with the runner-up.

Oliver had seemed a bit jealous, but that could very well be her seeing what she really wanted to see, nothing more. And even if the man was truly jealous, a whole lot of good it would do her if he had no intention on doing anything about it. Besides, he was still too angry at her for divulging his secret.

Felicity sighed as she remembered his outburst, barely minutes after regaining conscience in the basement. He had turned to her, seething with fury and disbelief in his eyes. Those stormy blue eyes of his told her he felt betrayed by what he clearly viewed as carelessness on her part, as if saving his life had been a mistake considering the price to be paid.

She could still see him, when she closed her eyes, turn around to her still out of breath and half trying to get his bearing, shit, the way he had looked at her...That face, with his emotions plainly written on his face, ripe for her to notice and get the full effect of what betraying him felt like.

" _You...You told him...Who I am..."_

He had said to her then and it hurt her, so much, to do that to him; with all they had been through. She never regretted saving his life though. True, she had made a choice, a difficult one at that with so much hanging in the balance of their secrecy. Her life, his secrets, his lies, their trust, the police, the possibility of jail for all of them...In the end, when they had to make a choice, she chose to save him. And she would do it all over again in a heartbeat. All of that meant nothing if he was dead.

After that, things got strained between them over again. She supposed Oliver still blamed her, probably still felt betrayed and things got rough for a while. Felicity had hoped he would forgive her transgression after a while, once some time had passed and he would realize she did the best she could given their circumstances. He had to see it was the only thing to do...

A day passed, then a week, two, and a month, but nothing happened. Their team suffered from it, with the Slade Wilson situation they had to deal with on the Arrow side and everything on the Queen Consolidated front, they were too busy for any heart to heart. Besides, since she had done the lifesaving - well not herself, but her choice did - she figured this time, the step should be his to take.

Yet neither the playboy/CEO wannabe nor the hooded vigilante would make a fucking step in the right direction. The last straw that broke her building frustration with him into a full blow anger happened a Monday morning.

Apparently while some of their team was working on their latest issues, some of them, and one particular someone had better things to do.

"Really Oliver? A red head this time?" She yelled as she threw the newspaper on his desk.

"What the-Felicity?"

She pointed towards the gossip section to her bewildered boss. In the middle was printed an enlarged, grainy picture of Oliver with a red head under his arm.

"I can't believe it...Do you have the slightest idea what I did last night, Mr Queen? Do you? Of course you don't...but I'm going to enlighten you..You...You...Pretty boy, playboy, CEO wannabe, arrow enthusiast slash maniac. I WAS HERE. Working my ass off last night, Oliver, searching for every little Intel on Slade Wilson. And for your information, after our all-nighter the day before, I was tired, ok? Exhausted if you really want to know. But I was still here, looking at it under every angle I could imagine...Now I know you're absolutely clueless about anything IT related...I'm not even sure you know how to play Angry Birds on your Phone so let's not talk about algorithms, Oliver. Algorithms. Do you even know what that is? And they search. For me. Well, for you actually, but...You know what I mean...It's not easy. I don't think you even know that. Do you think I just stare at my computers and look pretty, snap my fingers _et voila?_ Argh...I wouldn't even be surprised...That's what you really think I do isn't it? And you...You were...Out...Having fun with a...a fuc-"

"Felicity," he interrupted, smirking at the fury she unleashed on him.

His little tiger, clawing at him with all her might. Damn, she looked even better angry. He could just see himself throwing everything out of his desk to fuck her on it, but they had too much hanging on the balance for a quick, angry office fuck, no matter how much he wanted her right now. Things had been strained for a while between them. His intentions after Russia, to keep her at arm’s length for her own protection, were only reinforced by the Count when he held her hostage to get to him. He never hesitated a second before killing the man he had spared on their first encounter.

 _There was never any choice to make._ He had said it after she thanked him and still believed it. Much like her attitude towards Barry and their ensuing argument when his life was put on the line, he would do anything in his power to protect her. Anything.

Let that death be a lesson to any criminal out there who thinks they can get him through her. No one would be safe from his wrath if she was harmed because of her affiliation to the Arrow. No one. He would kill them all to save her, without any hesitation. The day after would never matter, nor would the toll the death took on him, if she was safe. Felicity was too important for him to make a mistake. He could argue that was why he had fucked Rochev, to fuck Felicity out of his system, and it was true to an extent. He could be man enough to own up to his mistakes and that night he had wanted the company, no matter how shallow it was. Though there was his lust too, like every human being it happened, he got horny, combined with that pumped up feeling coursing through his veins before a fight, half pent up anxiety and half excitement, so yeah, he fucked her. _It didn't mean anything._ Oh, he knew he had hurt her. And she did too. Felicity was trouble for him. Feelings complicated everything, he knew that, yet he couldn't help himself when it came to his blond genius. She was too unexpected, she threw him off balance, a feeling he tended to hate after so many uncertain days in his past.

"No, let me finish-" she stopped his thoughts short, about to start on another one of her rants.

"It's not what you think" He loved to hear her babble endlessly but right now, angry as she was, they were less amusing. And Felicity didn't know she was getting herself worked up over nothing. That photo had been taken a year at least before the Gambit's shipwreck, the woman must have been his fuck of the night and again, that didn't matter. Oliver Queen was no saint, he had plenty of sex back in the day; hell even nowadays, he could get anyone he wanted but the funny thing was those women lost their appeal.

"Oliver, I'm not blind-"

So, when Felicity started again, he shut her up. Literally threw himself at her like some eager teen and kissed the hell out of her. Just to be able to squeeze a word in. A faulty plan he would later realize.

Yeah, once they kissed, that didn't happen for a while. Talking was definitely overrated when you get what you want. And down the line, when their children would get onto him, he'd bribe them to not call any attention upon his super hero tactic as they would dub it. Oliver Queen would enjoy shutting Felicity up for many years to come. And though she feigned ignorance, she knew exactly what her favorite bow wielding billionaire was up to...

 

 

**Notes for the Chapter:**

> I always appreciate feedback. Good, bad or in between, I want to hear what you have to say.


	3. Chapter 3

**Notes for the Chapter:**

> I own nothing but my words and a strange taste for super heroes and islands. Everything else belongs to its rightful owner.

Felicity Smoak was a hard working woman. She never had an easy ride, contrary to Oliver Queen, whose family could build a new wing in whatever college he had wanted to apply in order to give his tumultuous records a fighting chance against straight As students. Felicity's parents had no means to grant her entry to a good school, only her intellect and the scholarship she had earned had allowed her to attend MIT and become their top graduate.

She was fine with it, knew that was the way the system worked, double standards for the rich and the others, for the elite and regular people, always had and always will. So, she had fought for her future, no matter how hard it was sometimes to study in her small dorm room or how difficult it was to balance her studies with her part time job. A MIT scholarship, however well-funded it might have been, had no stipend for clothes or her computer addiction. Those were extras she needed in order to blend in with the elites of the country and she worked hard to get them.

Her first job at QC had been earned on her curriculum, and she had made her way to the top entirely due to her achievements in the IT department of the company, not because she had slept with a sleazy head hunter like one of her colleague or because her mommy knew someone on the board. However, her dedication to her work, the long hours she put in without saying a word and the quality of her work were recognized by her superiors and slowly, even Mr. Steele became aware of her work. He called her regularly to get her opinions on the latest software development or anything IT related that could improve his wife's company.

When Oliver, the long lost Queen heir came back to civilized life, after a five year stint on a deserted island, she knew of course, nobody in the city could escape the news but a hermit, as it had been all over the news ever since the former playboy had reappeared. Felicity never anticipated much more would come from that, sure she worked for his family, but so did a thousand other people and more, she figured the most she'd see of him would probably be through the latest gossip at work or in the news, hell, maybe she'd bump into him if he ever came to QC, but that's it.

She never imagined, in her wildest dreams, that the reformed playboy had would turn into a bow wielding vigilante on a crusade to right his father's wrongs, much less that he would handpick her to be his trusted IT genius. Yet he did. And she became a part of his team, they worked together with Diggle to save their city from the Undertaking -and failed but still saved hundreds of lives in the process- and so forth, weathering every storm looming over the safety of Starling City's civilians or threats from within, what with the rampant corruption of most politicians and the greedy elites.

What she had never expected, however, was to suddenly become the focus of the gossip mill. She was always the straight laced student, save for a few drunken nights in college, never made waves at work, did everything by the books, her records -both professional and personal- were spotless.  
Thanks to Oliver's latest brilliant plan, she had apparently become a person of interest for every gossiping old secretary at work and don't even get her started on all the jealous tramps and their sisters. Everyone had it in their crazy, perverted minds, that she somehow got her promotion by sleeping her way to the top, particularly by fucking one billionaire heir it seemed. 

She should have seen it coming, perhaps, yet when Oliver told her about his EA scheme, the only thing she had seen was the secretary tidbit. That had registered, she had been insulted by his proposition, after all who in their right mind would see that so called promotion as such? She was a MIT graduate, for fuck's sake, and had told her infuriating boss as much.

He had tried to be cute about it, telling her he needed a "girl Wednesday" which she had found only increased her anger at the clueless man. "It's Friday! And the answer is NO!"  
Obviously not in the mood for such a confrontation, he had to refrain his first thought, bite back on his answer and turned to show her the new computers she was to use.  
"These computers have been upgraded. Far more processing power than your typical secretary."

As if he could sweeten the deal for her with a couple of high powered computers...Okay, so maybe it wasn't a bad move on his part, but Felicity was much too infused to see a rational side in his actions that day. When he had dismissed her concerns and their argument altogether with a wave, turning his back to her thus ending their face to face confrontation and walked back to his office, she had followed him to counter his point.

"Did you know I went to MIT? Guess what I majored in? Hint: not the secretarial arts."

"Felicity!" he had tried to calm his furious blonde genius and appeal to her reasonable side. "We all need to have secret identities now. If I'm going to be Oliver Queen CEO then I can't very well travel down eighteen floors every time you and I need to discuss how we spend our nights!"

"And I love spending the night with you..." Of course, it was too much to ask for her not to babble with innuendo during their little showdown.

She closed her eyes in frustration and counted backwards to calm herself. "3...2...1..."

She continued without looking at her aggravating boss, trying to put some distance between them and keep on point. "I worked very hard to get to where I am, and it wasn't so I could fetch you coffee!"

Oliver had simply rolled his eyes at her, buttoned his suit back before walking towards his desk. Once seated, he had deemed their conversation over to focus back on the issue at hand, she had sighed and Diggle had sarcastically declared "well it could be worse, my secret identity is his black driver", trying to make her see some positive in the whole fiasco and defuse the situation.

As far as Oliver knew, this conversation had ended right there and they had moved on.

Except she had not. 

She was still hurt over the matter, having lost her position in the IT department in favor of being Oliver's glorified secretary simply did not cut it for her. Besides, he should never have taken such a decision, one which would have that much impact on her real life without talking with her first.

He had seen what was more convenient for him, for Oliver Queen CEO-The Arrow. Not what was best for her, and it hurt. Sure, maybe she was making a fuss over something not so important in regard with the life threatening circumstances they faced every night but it was her livelihood, for fuck's sake. How could he expect her to merely see his point and basically think well okay, yes, that's the best course of action?!

The man was so obvious he would not have recognized her indignation for what it was if it came and bit him in the ass. Felicity was a grown up, a responsible woman, she paid her bills on time, never owed any debt to anyone, had made her way up on the ladder with her hard work and personal qualifications and she intended for it to stay that way.

Later that night, at the Foundry, he had been working out on his salmon ladder, offering her the best view of the city. She wasn't oblivious, she knew exactly what the man was doing, trying to use his physical prowess to distract her and she told him as much.

"I know exactly what you are doing, Oliver Queen, so don't bother."

He chuckled and smiled at her. "Oh yeah, and what is that, Miss Smoak?"

"You're trying to distract me" she retorted as she watched his abdominal muscles ripple with the effort he imposed on his body. With every pull of the bar, every climb up he made on the ladder she could see the strain it imposed on his arms, his abs, every single of his upper torso muscles would stretch the relax slightly only to tense again with the next climb he made.

The man was magnificent and he knew it.

"Give a girl a break, Oliver. No matter how much time you spend on it isn't going to miraculously erase my anger, though I do appreciate the view, don't get me wrong...But you went too far, that isn't an easy fix situation, Oliver, don't you get why I'm mad? You messed with my life, Oliver, my life! My work was never supposed to be on the line. In fact, I was perfectly happy being your IT go-to genius in the shadows. It was never...I didn't...Arggh...See? I'm still angry hours later, Oliver, and that won't go away. I worked hard to get where I was, I have work dedication, Oliver, and you just threw a decade of hard work down the drain, so forgive me for being frustrated with you...Hell, I'm angry..."

"Felicity, look..." he jumped to the ground and approached her slowly, as one would with a wild animal. He stood before her desk, trying to catch her eyes and make her understand why it was such an important part of his plan, why she was such a trusted, crucial piece of his puzzle.

"I know I overstepped-"

"You think? I was on my way to supervise the whole department, Oliver, I had a great start to what used to be a promising career...and now I'm what? That blonde in skirt who will fetch you coffee in the morning, take notes for you in meetings and schedule your appointments? It's not-"

"I know it's not ideal, Felicity, fuck I know you would've never gone for it if not for me. But I need you, Felicity. I trust you, don't you see? When I had to choose someone to be on my side, someone who I could blindly trust, someone who would not end up backstabbing me in the back when I have a minute of inattention...There was no choice to make. I need you to do this for me, Felicity. Our night activities will be much easier if you are by my side and it's more than that. I need you with me as my right hand woman, my girl Friday or whatever you want to call it, but I need you to help me save my family company in addition to the city. Will you help me, Felicity? Will you stand by me?"

Gradually easing into a crouch in front of her, Oliver had taken her hands in his and had delivered his heartfelt speech while staring into her eyes. And what was a girl to do besides nod and reassure the man that she would indeed stand by his side in his crusade, whether it be as the Arrow or as CEO?

After that night in the basement of Verdant, things had progressively returned to normal between them. They took down China White, Bronze Tiger and the Doll maker, rescued Laurel and Diggle's ex wife, unfortunately freeing Floyd Lawton aka Deadshot in the process.

Their next bone of contention happened to be Isabel Rochev. Oliver had carelessly slept with her during their stint in Russia, to Felicity's complete and utter disbelief.

She understood sexual needs, hell she had a healthy libido herself but could not comprehend why the infuriating man chose this one in particular to fuck.

"Over 64 million of women over the age of consent in Russia and you slept with her?"

Oliver had blinked at her and paused before answering uncertainly to her. "So we're not doing the ‘whatever happened in Russia stays in Russia?’ "

"We're still in Russia!" she exclaimed, outraged at his half assed answer.

She would have been fine with him fucking anyone in Russia, from leggy blond models to voluptuous red heads but no, he had to sleep with Isabel fucking Rochev. If he liked the danger, she would have been perfectly able to point a loaded gun at him herself.

Nevertheless, they had moved on from that too and her anger had shifted from her new job to his choice of fucking partners in a few hours. After a few days, that had passed too, her moods had slowly diffused and things had gotten more or less back to normal. There were still awkwardness in their interactions and her feelings to deal with but they managed. He had made his position clear to her, post Russia gate.

"Because of the life that I lead", he had told her with his stormy blue eyes solely focused on her, he would not "let himself be with someone that I could really care about" and though she was hurt, she resigned herself to soldier on for their crusade, because it was that important for the people of their city. 

There was much more at stake than just her feelings. She felt hurt, frustrated and still a bit angry with Oliver, but she moved on for the greater good, as cliché as that was. The Arrow was too important for her to fuck up with petty sentiments, not to mention that her resident billionaire never gave her much more to go on concerning his feelings. Besides a heated look here and there, some innuendos if she blinked very hard and his obvious yet contained jealousy at the Barry Allen's debacle, she could never tell if it was all in her head and she was seeing things that were simply not there or if she stumbled upon a true hint of what he could feel.  
The first time he asked her to stand by him, that night in the basement of Verdant, her heart had stuttered at his words. He had asked her to take her stand by his side, and she had said yes, without any doubt or regret.

And she would. Always. Because she believed in him, she had seen through him right from the start and his ridiculous lies about bad neighborhoods, suspicious bullet holes he pretended to be latte spills, false forlorn friends, and so forth. She went on the wild goose chases he put her up to on his vigilante alter ego's behalf precisely as a result of the nagging she felt in her gut, that instinct which told her he was a good man, despite the appearances, and that she could trust him.

And so far, he had not caused her to be upset over her choices, until her promotion -demotion, thank you very much, she would say- and his subsequent apology, then plea, that following night.

Ever since that night she had been out of sorts. She replayed their conversation down to his smile, his eyes and how they held her captive under their heavy gaze. Felicity knew she was being perfectly ridiculous, she behaved like a silly teenager with a crush on a celebrity and that was not her style. Yet this man, this infuriating, extraordinary, maddening, incredible man had a hold on her, whether she liked it or not.

She watched him from time to time, between two appointments set in his calendar through the glass separating them. Oliver Queen, in all his glory, sat there at his desk, watching the darkening sky while doodling on a blank page. He was beautiful. Truly. He would probably be upset over her description, just like every manly man, but he was. For all the burden he had to bear on his shoulders, there were still moments when she would catch him marveling at the world he had come back to. He was almost like a child, taking in the world around him, as if he saw it for the first time, which was probably a consequence of his island past she thought. You never fully appreciate what you have until it's gone and when you get it back it feels like being able to breathe again, to be free once more.

Getting up to make coffee in their break room, she glanced backwards and smiled at him when he noticed her movements. She headed down the hall and was about to turn at the corner of Isabel Rochev's office when she heard her talking with two executive assistants.

"Can you imagine something more cliché than that?" the she-devil Oliver had the poor taste to bed asked in her usual condescending tone to her colleagues.

"I've heard from a friend in the IT department that she pined over him for months. They say he came down to fuck her in the backroom whenever she had a break" added Isabel's secretary.

"Oh my god, I knew she was a slut, but she really has no self-respect."

"Did I tell you about our trip to Russia? She spent half the time in the bathroom sucking him off from what I could gather from where I sat."

For the love of...Those people...and that woman! She never did anything in the plane ride back from Russia but glower at Oliver the whole time. And Rochev knew that perfectly well, she was seated between them...That dishonest, backstabbing, self-entitled bitch spewed her venom everywhere she went, so really, Felicity should have been more surprised that she had not yet stooped to that level.

She sprinted back to their office and bumped into Diggle who stood idly by her desk. He took one look at her, saw the furious glint of her eyes and made a hasty retreat, telling her he was going down to check on something.

Finally, they were alone. She went inside Oliver's office, locked the door and drew the shades with the remote control. She turned towards him and saw his bemused look at her demeanor, she inhaled then whisper yelled at him.

"Oliver"

He went stiff but softly answered her, “Felicity?"

"Did you know?"

"Did I know...what?"

"Isabel...fucking...Rochev is telling people that-"

"For fuck's sake, what has she done now?"

"She's telling her colleagues...our...my colleagues that I gave you a blow job on the plane ride back from Russia...in the corporate jet, Oliver. In the bathroom of QC's very own private plane-"

"She WHAT?" Oliver, who had just drank a mouthful of water spat it back, spluttered and coughed.

Felicity rushed back to his side and started patting his back as he coughed. "Oh my god are you OK? Don't panic, breathe, cough, do whatever you have to do but don't die on me, Oliver. I can't be the tramp who screwed the boss, sucked his cock in the airplane and killed him in his office..."

He grinned at her and took hold of her wrist, bringing them to his chest as he regulated his breathing.

She flushed from head to toe, her face flaming a bright red when she realized the position they were in. His movement had brought her almost on his lap, still balancing her feet on the ground with her legs outstretched and her ass hovering over his groin as he turned her to face him.

"What...Oliver? What are you doing?"

"I'm trying something" he rasped.

"But why? Why now? You said you couldn't..."

"Because I'm tired of pretending, because I'm frustrated every day and every night and because people already think we're sleeping-"

"Fucking, Oliver...full blown on dirty sex in crazy places, that's fucking, not sleeping together...and on company time, Oliver. I don't particularly care about other people but that's work, Oliver... I used to have a reputation at work, people respected my work. Now I'm the slut who sucked you off in your private jet. I'm a MIT graduate, Oliver, did I already tell you that? I'm pretty sure I did. And now-"

"Calm down, Felicity, breathe. In and out. Look at me. That's it, calm down."

After catching his eyes she started to relax. He rubbed his thumbs on her shoulders, back and forth in a soothing manner. She started to think about what it meant. She wanted him to say sorry, maybe promise that he would correct Rochev's lies but she was not expecting him to want more. Not right now, at least, not so soon after his self-sacrificing declaration earlier that month. She did not truly know where they stood now that they had almost crossed the line between them and that was unsettling for Felicity. What if he changed her mind? He had decided a relationship with her was not on the table yet here he was, practically giddy like a teenage boy, promising her things she was not convinced he would not regret once his current mood switched back to his usual brooding. She could not start to let herself believe in them if he wasn't sure. She voiced her doubts to Oliver who snorted at her.

"I'm not going to change my mind, Felicity."

"Oh yeah? And how am I supposed to know that, Oliver? Don't you remember, six months ago, when you were still pining over Laurel? That was not so long ago, Oliver...What guarantee do I have that you won't change your mind in three months? You told me she was the love of your life, for fuck's sake. The love of your life, Oliver. How am I supposed to compete with that? I don't ever want to be compared to her, I don't measure up Oliver and it's only a matter of time before you realize that. And then what? I'll be heartbroken, you'll be you and probably reconcile with Laurel while I watch from the sidelines...And I can't. I can't have you only to lose you a few months later. I can't Oliver, please, don't ask me to do that. That's cruel, even for you-"

"I am not going to change my mind, Felicity-"

"You've said that already, but you don't know that. You're flighty, Oliver, one day you're giving me subtle touches, innuendos and longing looks while the next you'll give me the cold shoulder and tell me you're too dangerous for me. What am I supposed to make of that,huh?"

"You want an explanation? Fine. How's that? I've been thinking about what I said to you, ever since that day. And I regret it, ok? I've realized that you're in danger no matter what I do, whether you get hit by a car tomorrow or fall down the stairs...There are so many things that could hurt you...And while I could not prevent them all, I thought that the least I could do was to protect you from what I could actually anticipate. People are always going to want to hurt those I love as long as I'm the Arrow, fuck even as Oliver Queen CEO I have plenty of enemies, Felicity. And I did not want to expose you to that. But ever since that day, with a few nudges from Diggle, I started to think about all the danger you already face...and I...I'm tired of stopping myself, OK? Look, I probably feel like you right now, rambling about what's in my head. And God knows I've never been the talk about your feelings type, Felicity, but...if you still want to? I'd like to try-"

"Of course I still want to. I'm still here, aren't I?"

He smiled at that and exhaled before framing her face with his hands, tilting her head back to gaze at her flushed face.  
"You are remarkable, Felicity Smoak, did I ever tell you that?"

"Once or twice, but feel free to tell me as frequently as you wish. And know that it's the same for me. I find you extraordinary too, Oliver. Always has, always will. You know that. And however much I love to hear you say that...which believe me, is a lot, I've been fantasizing about you saying those things to me for a while...but...-"

"Shut up, Felicity and kiss me" he smiled again at her and leaned in "do it, Felicity, trust me. Do you?"  
She blushed deeper -and yes, that is possible, she could actually turn several deeper shades of red when she reddened- before answering him.

"You know I do. Always."

And she bridged the gap between them, molding her lips to his. He bit her bottom lip, earning a gasp from his favorite blond genius sidekick and hauled her completely on his lap. She moaned as he entered her and explored her mouth thoroughly with his tongue, tangling with hers, dominating her with his firm strokes and guidance. She should have known that Oliver Queen never did anything half way. The man was a languorous kisser, she felt dazed, a bit confused but most of all she felt desire. Oliver put his hand under her thighs and lifted up with her, clearing the mess on his desk with a brush of his right hand and laying her on it.

"Oliver-"

"Shh"

She moaned again, trying to regain some form of consciousness while the man was doing wonderful things to her mouth. He had skills, she'd give him that. She was half way thinking about every one of his former conquests and reaching out to thank them for providing him with a target practice.  
She pushed at his chest with her hands and he gave her that smoldering gaze of his.

"What?"

"Seriously, Oliver?"  
He smirked smugly and asked "did I misread that and missed the part where you were not enjoying yourself?"

"You know I did, but Oliver-"

"No buts, Felicity. Are you in? Will you stand by me?"

And just like the last time, she could do nothing but nod before leaning back for another one of his mind blowing kiss. Fuck the job, fuck Rochev. She was not letting go of that man, flaws, scars, arrows; she would take it all. For him. Because he asked and he needed her and hell, because she had enough imagination to keep them going for a while.

First would come the desk, then the basement, maybe the Queen mansion next, but for obvious reason at the top of her list was the thought of being fucked by the Arrow. Go figure...

The next time Oliver would ask Felicity to stand by him would not come until many years later. He would surprise her in their office through a wild goose chase on the Internet, leaving her little clues here and there throughout the world wide web to get her where he wanted her, on a private stream Diggle's ex-wife Lyla -whom he had finally remarried after two years of dancing around the issue- had set up for him. Oliver had prepared a little sideshow for his genius tech after she cracked the inscription's code. Pictures of them were following articles dubbing the Arrow a hero. At the end of which stood Oliver, in front of her old office down the eighteenth floor, his face alight by mischief.

"I'm so proud of you, Felicity, but I knew you'd get there. I thought you'd appreciate the theatrics. I know you've recognized your old office. Where it all started, where we met..." Oliver rasped, obviously choked up with emotion, his brilliant blue eyes turning stormy "and you changed my life, Felicity...just as I did yours. I wanted to ask you something. I know, I know, we talked about my billionaire antics, and while I could point out that our QC stocks have never been that high, I just want you to indulge me this time. So don't be mad, besides this hasn't cost me...much. I called in a favor with Lyla so..." he winked at her as he grinned at the camera. 

God, he was such a good looking man. Her extraordinary islander, CEO, vigilante, her life partner...What was he up to now?  
On screen, Oliver pointed towards a laptop laying on her former desk.

"That's where you will find the next piece of the puzzle, Felicity so come get your present my love."

She closed the feed and headed towards the elevator. She pushed the button to go down to the eighteenth floor, feeling a sudden bit of nostalgia come to her as she thought of their past. For all the hurt it had brought her, it also gave her hope and happiness. Years after their first meeting, she had yet to regret the path it had put her onto. As she entered her desk, she was surprised to find it empty, she had thought Oliver would be waiting for her but the only thing greeting her was the laptop she had seen on the video feed. Cracking a few minor codes to open the software, she found it empty. Running different analyzes on the computer, she finally discovered a single hidden file. On it were two lines of binary code, two simple phrases for someone like her. She struggled to believe what she read as she realized the meaning of the little quest Oliver had put her up to.

"Will you stand by me, always?" said the first line in the file. 

Felicity felt arms enveloping her waist from behind and felt her boyfriend breathe at the back of her neck, kissing it lightly before laying his chin on her shoulder.

"Well?"

"You do know what is written there, right? It's not one of your 'let's experiment and try binary code' like you did with the poisonous coating of your arrows right? Because I'm not sure I can take that, Oliver, I...I don't know what to say, I mean...I'm not supposed to get that...Happy ending, Oliver, really...You know it's a cliché, right, the secretary with the CEO and people-" Oliver chuckled, kissed her cheek and turned her in his arms.

"I know what it means, genius mine. And you were never a secretary. Will you?" Felicity smiled, looked backwards to the laptop, read the second line for the 5th time before turning to look at her favorite arrow shooting billionaire and answer him

"Yes, I will marry you Oliver, and I'll stand by you. Always." He let out a nervous laugh and smiled at her, catching her lips in a heated kiss once more.

"You're worse than a Chinese interrogator for my heart, tian xin"

"Don't you forget it, Oliver Queen" she joked. "Don't fail me or I'll sick the Arrow on you, I have it on good authority that he hates when I get hurt."

Many months later, Oliver Queen would end up tied to a chair with his fiancée in full Arrow get up, hood on, bow in her hand, telling him the Arrow had failed their evening...

Best role play sex ever.

**Notes for the Chapter:**

> I always appreciate feedback. Good, bad or in between, I want to hear what you have to say.

**Author's Note:**

> I always appreciate feedback. Good, bad or in between, I want to hear what you have to say.


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